A convenient synthesis of racemic and optically active 1-aza-1,3-dienes derived from γ-amino esters: reduction to α,β-unsaturated and saturated γ-amino acid derivatives

A simple synthesis of racemic and optically active 1-azadienes derived from γ-amino esters by olefination reaction of alkyl glyoxylates and functionalized phosphonium salts or phosphine oxides is reported. Selective reduction of these 1-azadienes with hydrides yields (E)-γ-amino-α,β-unsaturated esters. A simple procedure for the preparation of saturated γ-amino acids and γ-amino esters from the previously synthesized vinylogous amino esters is also described.